| Title: | "Synthesis and bioassay of racemic and chiral trans-alpha-necrodyl isobutyrate, the sex pheromone of the grape mealybug Pseudococcus maritimus" |
| Author(s): | Zou Y; Daane KM; Bentley WJ; Millar JG; |
| Address: | "Department of Entomology, University of California, Riverside, California 92521, USA" |
| ISSN/ISBN: | 1520-5118 (Electronic) 0021-8561 (Linking) |
| Abstract: | "A concise synthesis of the racemic form of the female-produced pheromone of the grape mealybug was developed. The synthesis was readily adapted to production of both enantiomers of the pheromone via lipase-catalyzed kinetic resolution of an intermediate in the synthesis. Replicated field trials revealed that, contrary to a preliminary report, the (R,R)- rather than the (S,S)-enantiomer is the attractive stereoisomer. Lithium aluminum hydride reduction of the insect-produced compound to alpha-necrodol followed by analysis on a chiral stationary phase GC column showed that the insect-produced material was actually an 85:15 mixture of the (R,R)- and (S,S)-enantiomers. The racemic form of the pheromone was highly attractive to male mealybugs, and in one of two field bioassays, the racemic material was significantly more attractive than the pure (R,R)-enantiomer, suggesting that the (S,S)-enantiomer might act synergistically" |
| Keywords: | Animals *Biological Assay Butyrates/*chemical synthesis/*pharmacology Female *Insecta Kinetics Magnetic Resonance Spectroscopy Male *Sex Attractants Stereoisomerism; |
| Notes: | "MedlineZou, Yunfan Daane, Kent M Bentley, Walt J Millar, Jocelyn G eng Research Support, Non-U.S. Gov't 2010/04/02 J Agric Food Chem. 2010 Apr 28; 58(8):4977-82. doi: 10.1021/jf904452v" |
